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Method for preparing Beta, Gamma unsaturated ester

A technology of unsaturated and conjugated olefins, applied in chemical instruments and methods, preparation of carboxylic acid esters, preparation of organic compounds, etc., can solve the problem of low catalyst system efficiency, low selectivity of catalyst system, low yield of target products, etc. question

Active Publication Date: 2007-07-25
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The specific results are as follows: in U.S. Patent No. 5,028,734, the yield of methyl 3-pentenoate is 75%, and a certain amount of methyl 2-pentenoate is by-produced simultaneously, so the selectivity of the catalyst system is not high; U.S. Patent The conversion rate of butadiene in No. 5,495,041 has only about 80%, and the selectivity of 3-pentenoic acid methyl ester is below 50%, so the target product yield is low; And the selectivity of methyl 3-pentenoate is about 92%, and the TOF value of the catalyst system used is all at 212h -1 , below, so the efficiency of the catalyst system is low; U.S. Patent No. 6,232262 also has the problem of low yield of 3-pentenoic acid methyl ester, the highest yield is 75%

Method used

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  • Method for preparing Beta, Gamma unsaturated ester
  • Method for preparing Beta, Gamma unsaturated ester
  • Method for preparing Beta, Gamma unsaturated ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Under nitrogen protection, 0.05mmol palladium acetate, 0.11mmol αα'-bis(diphenylphosphino)phenyl ether (Oxydi-2,1-phenylene)bis(diphenylphosphine), 328.00mmol methanol, 0.718g n- Nonane (internal standard) and 50ml diphenyl ether or anisole, then add 286.50mmol 1,3-butadiene, and fill with carbon monoxide to a pressure of 5MPa. The reaction was stirred for 4 hours in an oil bath at 230°C. After the reaction was completed, it was cooled to room temperature, and the product was analyzed by gas chromatography-mass spectrometry. The results showed that 1,3-butadiene was completely converted, the selectivity of 3-pentenoic acid methyl ester (3-MP) was above 96%, and the gas chromatography yield was 96%.

Embodiment 2

[0031] Under nitrogen protection, in 250ml autoclave, add 0.05mmol palladium acetate, 0.4mmol αα'-bis(diphenylphosphino)phenyl ether, other reaction conditions are the same as embodiment 1. After the reaction was finished, it was cooled to room temperature, and the product was analyzed by gas chromatography-mass spectrometry, and the gas chromatography yield of methyl 3-pentenoate was 84.8%.

Embodiment 3

[0033] Under nitrogen protection, add 0.05mmol palladium acetate, 0.06mmol αα'-bis(diphenylphosphino)phenyl ether, 328.00mmol methanol, 0.072g n-nonane (internal standard) and 10ml anisole in 250ml autoclave, then Add 286.50 mmol of 1,3-butadiene, and fill with carbon monoxide to a pressure of 3 MPa. The reaction was stirred for 4 hours in an oil bath at 230°C. After the reaction was completed, it was cooled to room temperature, and the product was analyzed by gas chromatography-mass spectrometry, and the gas chromatography yield of methyl 3-pentenoate was 35.4%.

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Abstract

This invention discloses a method for preparing beta-gamma unsaturated ester from conjugated olefin. The method adopts conjugated olefin, CO and hydroxyl-containing compound as the raw materials, as well as palladium compound and diphosphine compound as the catalysts. The raw materials react in nonpolar or weak polar solvent to obtain beta-gamma unsaturated ester. Under optimized reaction conditions, the conjugated olefin can be converted completely, and the selectivity of the target product is higher than 96%. Besides, the catalysts can be recycled, and the TOF value of the catalyst system in a single use is up to 1432 h-1.

Description

technical field [0001] The invention relates to a method for preparing β-γ unsaturated esters by carbonylation of conjugated olefins. Specifically (but not limited thereto), the present invention relates to 1,3-butadiene, carbon monoxide and methanol as raw materials, with a palladium compound and a bidentate phosphine compound as a catalyst, in a non-polar solvent or weakly polar solvent Reaction, the method for preparing 3-pentenoic acid methyl ester. Background technique [0002] In recent years, major foreign chemical companies and some research institutes (such as DSM, Shell, DuPont, BASF, and Taiwan Industrial Research Institute, etc.) have actively improved the existing technical route for the production of caprolactam, and have carried out research on the production of caprolactam. The research on the production of caprolactam from alkene as the starting material has achieved certain results. Among them, the Altam route jointly developed by DSM Company and Shell Co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B41/12C07C67/00C07C67/38C07C69/00C07C69/533
Inventor 余正坤吴小伟
Owner CHINA PETROLEUM & CHEM CORP
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